반응 #169460

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(5-Bromo-pyridin-3-yl)-{7-[1-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-methanone

ammonium hydroxide

→

title compound

수율 45.0%

(5-Amino-pyridin-3-yl)-{7-[1-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-methanone

수율 45.0%

용매

1-Methyl-pyrrolidin-2-one

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   추출extracted with 10% methanol in dichloromethane (5×25 mL)
3. 3
   건조The combined organic layer was dried over sodium sulphate
4. 4
   기타evaporated in vacuo
5. 5
   기타The crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 96:4)

실험 절차

To a stirred solution of (5-Bromo-pyridin-3-yl)-{7-[1-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-methanone (Preparation 250, 200 mg, 0.45 mmol) in 1-Methyl-pyrrolidin-2-one (1.5 mL) was added ammonium hydroxide (15 mL). Then copper (I) oxide (3 mg, 0.02 mmol) was added and the reaction mixture was heated in a sealed tube at 130° C. for 16 hours. The reaction mixture was cooled to room temperature, extracted with 10% methanol in dichloromethane (5×25 mL). The combined organic layer was dried over sodium sulphate and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (gradient of dichloromethane:methanol 100:0 to 96:4) to afford the title compound as a white sticky solid in 45% yield, 80 mg.

출처